US5376146A - Two-part aqueous composition for coloring hair, which forms a gel on mixing of the two parts - Google Patents

Two-part aqueous composition for coloring hair, which forms a gel on mixing of the two parts Download PDF

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US5376146A
US5376146A US08/112,162 US11216293A US5376146A US 5376146 A US5376146 A US 5376146A US 11216293 A US11216293 A US 11216293A US 5376146 A US5376146 A US 5376146A
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weight
group
lower alkyl
betaine
alkyl group
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Steve Casperson
Stanley Pohl
Michael Wong
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P&G Hair Care Holding Inc
Bristol Myers Squibb Co
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Bristol Myers Squibb Co
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Priority to US08/112,162 priority Critical patent/US5376146A/en
Assigned to CLAIROL INCORPORATED reassignment CLAIROL INCORPORATED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CASPERSON, STEVE, POHL, STANLEY, WONG, MICHAEL
Priority to CA002129473A priority patent/CA2129473C/fr
Priority to ZA945943A priority patent/ZA945943B/xx
Priority to TW083107253A priority patent/TW421598B/zh
Priority to JP23395794A priority patent/JP3284328B2/ja
Priority to AU71454/94A priority patent/AU687832B2/en
Priority to AT94113325T priority patent/ATE210420T1/de
Priority to DE69429393T priority patent/DE69429393T2/de
Priority to ES94113325T priority patent/ES2169055T3/es
Priority to EP94113325A priority patent/EP0640334B1/fr
Priority to CN94115715A priority patent/CN1070048C/zh
Priority to SG1996001493A priority patent/SG46242A1/en
Publication of US5376146A publication Critical patent/US5376146A/en
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/042Gels
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/416Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54Polymers characterized by specific structures/properties
    • A61K2800/542Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5424Polymers characterized by specific structures/properties characterized by the charge anionic
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88Two- or multipart kits
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/913Amphoteric emulsifiers for dyeing

Definitions

  • This invention relates to oxidative, aqueous, hair coloring compositions.
  • oxidation dyes of the type comprising primary intermediates and couplers are used in the dyeing of human hair
  • the procedure usually involves the use of a two part system.
  • One part is the lotion formulation which contains a variety of ingredients, including the oxidation dye precursors, and forms a gel immediately prior to application to the human hair, when mixed with the second part, the developer formulation containing a suitable oxidizing agent.
  • the developer usually contains an oxidizing agent, such as hydrogen peroxide and as a consequence some of the natural melanin pigment of the hair may be initially destroyed.
  • the precursors in the lotion penetrate into the hair and are oxidized to produce the desired color.
  • Such systems will generally contain 50% or more of organic solvents and surfactants, and require relatively high levels of dye precursors to produce the desired color.
  • the formulations must be stable to insure a reasonable shelf life.
  • compositions formed by mixing the lotion and developer must have theological properties whereby application, either by use of a brush or with the fingers, can readily distribute the dye throughout the hair mass and yet in the absence of stress, dripping or running from the hair during the color development period can be substantially avoided.
  • the dye mixture, as applied to the hair, should allow rapid diffusion of the dye precursors from the dye mixture into the hair fiber.
  • the mixture should preferably contain conditioning agents which leave the hair in a condition such that it is easy to detangle while wet and also feel smooth and be readily managed when dry.
  • the lotion and developer should preferably, but not necessarily, have comparable viscosities in order to facilitate mixing.
  • the dyeing effect should be rapid, with a dyeing time preferably under thirty minutes.
  • the reological properties have generally been attained by the use of a dye lotion containing a high level of surfactants and organic solvents to provide a thin lotion which, on mixture with a highly aqueous developer solution of the oxidizing agent forms a dye mixture with the desired gel-like consistency.
  • the disadvantage of this approach is that the dye mixture still contains a high level of surfactants which tend to retard the diffusion of the dye precursors into the hair.
  • the preferred surfactants in commercial products have been nonionic or anionic materials which do not provide any conditioning.
  • the preferred conditioners for human hair are cationic surfactants which provide excellent conditioning but are incompatible with anionic surfactants.
  • U.S. Pat. Nos. 3,303,213; 3,331,781; 3,436,167 and 3,891,385 describe the use in hair treating compositions of specific amphoteric surfactants such as the sodium salt of N-(N 1 , N 1 -dimethyl-aminopropyl)-N 2 -alkyl (fatty) asparagine wherein the "fatty" moiety is derived from the fatty acids of tallow.
  • the amphoteric surfactant can be employed with organic solvents and any of a variety of cationic, anionic or non-ionic surface active agents. There is no indication of the use of quaternary ammonium salts in the compositions.
  • U.S. Pat. No. 4,402,700 describes hair dyeing compositions containing quaternary ammonium compounds and also cites the possible uses of amphoteric surfactants in the compositions. These compositions, however, require the uses of organic solvents and nonionic surfactants, and the amount of water in the compositions is less than 50%.
  • U.S. Pat. No. 4,532,127 describes hair coloring compositions containing oxidative dyes together with an oxidizing agent.
  • the compositions require the presence of quaternary amine compounds containing two long chain alkyl radicals each having about 10 to 26 carbon atoms.
  • Any of a variety of surfactants may be present in the composition which, although they have a high water content may contain organic solvents.
  • the lotions of the patent contain di-long chain alkyl quaternary ammonium compounds in the presence of relatively large amounts of non-ionic surfactants. They are said to be superior to a comparison lotion containing a mono-long chain alkyl quaternary ammonium compound in combination with an amphoteric surfactant.
  • the lotions of this patent suffer from the disadvantage of having high levels of surfactant thus inhibiting rapid diffusion of the dye precursors into the hair. Furthermore, di-long chain alkyl quaternary ammonium are poorly biodegradable, particularly as compared to the mono-long chain alkyl quaternary ammonium compounds.
  • the compositions disclosed are free of anionic surfactants and anionic polymers.
  • U.S. Pat. No. 4,663,158 describes hair conditioning compositions containing an amphoteric surfactant together with at least one quaternary cationic polymer such as poly (methacrylamidopropyl)trimethy ammonium chloride sold under the trade name Clairquat-1.
  • the compositions are acidic.
  • U.S. Pat. No. 4,563,188 discloses hair dyeing compositions containing specific para-phenylenediamine derivatives which may contain any of several types of surfactants as well as organic solvents.
  • U.S. Pat. No. 5,137,538 describes oxidative hair dyeing compositions containing specific para phenylenediamines and N,N 1 diphenylalkylenediamines.
  • the compositions may be acidic or alkaline. They may contain organic solvents and anionic, cationic, non-ionic or amphoteric surfactants.
  • U.S. Reissue Pat. No. 33786 teaches that rapid dyeing with highly aqueous compositions can be achieved through the use of a certain acrylate copolymer viz an acrylate/steareth-20 methacrylate copolymer in the developer. Such polymers produce a thickening effect only when the developer is added to the alkaline lotion containing the color precursor.
  • the disadvantage of the use of acrylate copolymers, or any other anionic polymer is that they tend to deactivate quaternary ammonium conditioning compounds by complexation.
  • products containing a simple aqueous acrylate system are difficult to rinse from the hair.
  • experience has shown that lotions and developers containing the specific anionic copolymer of U.S. Re. Pat. No. 33786 are difficult to formulate in that the viscosity of the resulting mixture is not readily controllable.
  • compositions of the invention are readily rinseable from the hair at the completion of the color development stage and leave the hair in excellent condition.
  • This invention comprises a two part system comprising aqueous, oxidative, hair coloring compositions (lotions and developers) for mixture with each other shortly before use to form a gel.
  • the lotion comprises an aqueous alkaline composition having a pH of from about 7 to 11 and a water content of at least about 70% by weight, a tinctorily effective amount of oxidative dye precursors, an amphoteric surfactant and at least one monomeric quaternary ammonium cationic surfactant having one long chain alkyl substituent containing from about 10 to 26 carbon atoms.
  • the second part, i.e. the developer is an aqueous composition with a pH of from about 2 to about 6, preferably 2.5 to 4.5. It contains a peroxide oxidizing agent and at least one substantially water insoluble anionic acrylic polymer which is solubilized on admixture of the lotion and developer.
  • the components in the aqueous first part of the compositions of this invention include water, the oxidizable dye precursors, an amphoteric surfactant and a monomeric quaternary ammonium cationic surfactant having one long chain alkyl substituent.
  • the water content of the composition is at least about 70% weight and may be as high as 95% or higher.
  • compositions of this invention are in percent by weight based on the total weight.
  • Amphoteric surfactants belong to the category of surface active chemicals that possess a positive and a negative charge in the same molecule and behave as a cation or an anion depending on the pH of the medium. In general, the positive charge is located on a nitrogen atom while the negative charge is carried by a carboxyl or sulfonate group.
  • amphoteric surfactants that are suitable for use in this invention. They include, for example, the asparagine derivatives identified in the first three patents mentioned above as well as a variety of well known betaines, sultaines, glycinates and propionates which may be represented by the following structural formulas: ##STR1##
  • R is an alkyl or alkylamido group containing from about 10 to about 20 carbon atoms
  • R, R 2 and R 3 are alkyl or hydroxyalkyl groups, which may be the same or different, and contain up to about five carbon atoms and n is a positive integer up to about five.
  • amphoteric surfactants that are suitable for use in this invention include:
  • amphoteric surfactant or mixture of surfactants for use in this invention is not critical. They may be selected from amongst those suggested above, or from any of a number of other known amphoteric surfactants.
  • the amount of amphoteric surfactant in the compositions is normally from about 0.5% to about 15% by weight preferably 2% to 8% by weight.
  • amphoteric surfactants presently preferred for use in this invention are:
  • Cocamidopropyl betaine, coco-betaine, stearyl betaine, cocoamphocarboxyglycinate, cocoamphodipropionate, and stearoamphoglycinate Cocamidopropyl betaine, coco-betaine, stearyl betaine, cocoamphocarboxyglycinate, cocoamphodipropionate, and stearoamphoglycinate.
  • the pH of the lotions of this invention will generally be from about 7 to about 11. It is preferred, however, that this pH be in the range of 7.5 to 9.5.
  • any of a wide variety of alkaline reagents can be used to adjust the pH of the hair coloring compositions.
  • Ammonium hydroxide because of its freedom from toxicity over a wide concentration range and its economy, is an acceptable alkalizing agent.
  • any other compatible ammonia derivative as an alkalizing agent such as an alkylamine, for example ethylamine, or triethylamine; or alkanolamines, for example ethanolamine, diethanolamine, aminomethyl propanol, aminomethyl propanediol and trishydroxymethyl aminomethane.
  • any other of the organic or inorganic alkalizing agents may be used, such as sodium or potassium hydroxide, sodium or potassium carbonate, sodium phosphate, sodium hydrogen phosphate, sodium silicate, guanidine hydroxide and the like.
  • the preferred alkaline reagents are ammonium hydroxide, sodium carbonate and ethanolamine.
  • the selected pH will generally be achieved if the lotion contains from about 0.1% to 5% by weight of alkaline reagent.
  • the oxidative dye precursors employed in the practice of this invention comprise one or more primary intermediates together with one or more couplers.
  • the selection of specific intermediates or couplers determines the ultimate color of the treated hair. Such selection is not a critical aspect of the practice of the invention.
  • R 1 and R 2 which may be identical or different, can denote hydrogen, a C 1 -C 6 lower alkyl group, a C 1 -C 6 alkyl radical substituted with one or more hydroxy group(s) or with a methoxy, methylsulphonylamino or aminocarbonyl group, a furfuryl group, or a phenyl radical optionally substituted with an amino group
  • R 3 and R 6 denote, independently of one another, hydrogen, a C 1 -C 6 lower alkoxy group, a halogen atom such as a chlorine atom, a C 1 -C 6 lower alkyl group, or a C 1 -C 6 lower alkyl group substituted with one or more hydroxy group(s)
  • R 4 and R 5 denote, independently of one another, hydrogen, a C 1 -C 6 lower alkoxy group, a C 1 -C 6 lower alkyl group
  • 1 -C 6 alkyl group it being possible for the amino groups joined by the alkylene group to be substituted with C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl or C 1 -C 6 aminoalkyl; para-aminophenols; ortho-aminophenols; orthophenylenediamines, and heterocyclic oxidation bases.
  • p-phenylenediamine 2-methylparaphenylenediamine, 2-methoxy-para-phenylenediamine, 2-chloro-N-methyl-paraphenylene-diamine, N-furfuryl-para-phenylenediamine, 3-methoxy-N 1 -methyl-paraphenylenediamine, 2-chloro-paraphenylenediamine, N-methyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 5-chloro-N 1 -methyl-p-phenylenediamine, 5-methyl-N 1 ,N 1 -dimethyl-p-phenylenediamine, 5-methyl-N 1 -ethyl-N 1 -(amino-carbonyl-methyl)-p-phenylenediamine, 5-methyl-N 1 -ethyl-N 1 -ethylsulphonylaminoethy
  • the N,N 1 -diphenylalkylenediamines include, for example, N,N 1 -bis-(2-hydroxyethyl)-N,N 1 -bis(p-aminophenyl)ethylenediamine.
  • Their salts with acids such as the monohydrochlorides dihydrochlorides or sulphates are also suitable.
  • p-aminophenols which are usable according to the invention, there may be mentioned p-aminophenol, 2-methyl-p-aminophenol, 3-methyl-p-aminophenol, 2,3-dimethyl-p-aminophenol, 2,6-dimethyl-p-aminophenol, 3-methoxy-p-aminophenol, 2-chloro-p-aminophenol, N-methyl-p-aminophenol and 3-(methylthio)-p-aminophenol, of which p-aminophenol is preferred.
  • ortho-aminophenol 5-chloro-orthoaminophenol and ortho-phenylenediamine are chosen more especially according to the invention.
  • heterocyclic bases it is preferable, according to the invention, to use 2,3-diamino-6-methoxy-pyridine and 2-(2-hydroxyethyl)amino-5-aminopyridine and their salts, and still more especially 3,6-diaminopyridine, 2,6-dimethoxy-3-aminopyridine, 2-methylamino-3-amino-6-methoxypyridine, 2,5-diaminopyridine, 2-(N-hydroxyethyl)amino-5-amino pyridine, and 2-(N,N-bishydroxyethyl)amino-5-aminopyridine.
  • More especially preferred primary intermediates are p-phenylenediamine 2-methyl-p-phenylenedamine, N-(2-methoxyethyl)-p-phenylenediamine, N,N-bis(2-hydroxyethyl)-p-phenylenediamine and p-aminophenol.
  • R 1 denotes hydroxy or an amino group which can be substituted with one or more C 1 -C 6 hydroxyalkyl groups
  • R 3 and R 5 independently of one another, can denote hydrogen, a hydroxy group, an amino group optionally substituted with a C 1 -C 6 lower hydroxyalkyl group or a C 1 -C 6 lower alkyl group
  • R 2 , R 4 and R 6 can denote a hydrogen atom or a C 1 -C 6 alkoxy group, a hydroxyalkoxy group or a C 1 -C 6 lower alkyl group; it also being possible for R 3 and R 4 together to form a methylenedioxy group.
  • 2-methoxy-5-aminophenol 2-methoxy-5-[N-(2-hydroxyethyl)amino]phenyl
  • 1,3-diamino-2,6-dimethoxybenzene 2-methoxy-1-(N-methylamino)-4-(2-hydroxyethoxy)-3-aminobenzene
  • 1,3-diamino-6-methoxybenzene 1,3-diamio-4,6-dimethoxybenzene
  • 2,6-dimethoxy-3-[N-(2-hydroxyethyl)amino]-1-aminobenzene 2,6-dimethyoxy-3-[N-(2-hydroxyethyl)amino]-1-aminobenzene
  • Couplers are 6-aminobenzomorpholine, 1-amino-7-naphthol, 6-hydroxybenzomorpholine, 1-naphthol, 1,3-dihydroxynaphthalene and 1,2-dihydroxy-benzene.
  • heterocyclic couplers there may be mentioned 2,6-dihydroxypyridine, 2,6-diaminopyridine, 2-amino-4-hydroxypyrindine, 2-hyroxy-4-amino-pyridine, 2-hydroxy-5-aminopyridine, 2-amino-6-hydroxypyridine and the like.
  • 2,6-diamino alkyl pyridines where the amino nitrogen of one or both amino groups is mon- or distributed with a C 1 -C 6 alkyl group such as the methyl, propyl, isopropyl, butyl, iso or sec-butyl, pentyl, sec-pentyl neopoentyl, t-butyl, hexyl, 3-methyl pentyl or 4-methylpentyl groups.
  • the amino groups of either the amino-4-hyroxy- or 2-hydroxy-4-amino-pyridines may also have mon- or d-C 1 -C 6 alkylation on the nitrogen atoms.
  • the 2,6 amino-, or 4-amino-2-hydroxy- or 2-amino-4-hydroxy pyridine nitrogens may also either singly or doubly be derivatized with alkoxy substituents of carbon lengths of 1 to 6 with specific mention of 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl, 5-hydroxypentyl, 6-hydroxyhexyl, 2-hydroxypropyl, 2-hydroxybutyl, 2-hydroxypentyl, 2-hydroxyhexyl, 3-hydroxybutyl, 3-hydroxypentyl, 2-hydroxyhexyl, 4-hydroxypentyl and 5-hydroxypentyl groups.
  • 1,2,4-trihydroxybenzene 1,2,4-trihydroxy-5-alkylbenzenes in which the alkyl group is a C 1 -C 6 lower alkyl group and 1,2,3-trihydroxybenzene, and their salts.
  • diaminohydroxybenzenes there may be mentioned 2,4-diaminophenol and 2,5-diamino-4-methoxy-1-hydroxybenzene, and their salts.
  • aminodihyroxybenzenes there may be mentioned 2-amino-1,4-dihydroxybenzene, 1,4-dihydroxy-4-diethylaminobenzene and 4-aminoresorcinol, and their salts.
  • substituted 1,2-dihydroxybenzenes 4-methyl-1,2-dihydroxybenzene and 3-methoxy-1,2-dihydroxybenzene are especially preferred.
  • aminohydroxybenzenes are chosen, in particular, from 2- amino-4-methoxyphenol, 2-aminophenol, 4,6-dimethoxy-3-amino-hydroxybenzene and 2,6-dimethyl-4-[N-(p-hydroxyphenyl)amino]-1-hydroxybenzene, and their salts.
  • N-acetyl dopa is N-acetyl dopa.
  • the primary intermediate(s) and coupler(s) in the aqueous lotion of the invention will normally be employed in equimolar quantities, each at a concentration of about 0.0005% to about 5% by weight, preferably 0.005% to 2.5% by weight.
  • the quaternary ammonium salt employed in the lotion part of the composition may be selected from any of a number of known monomeric salts including those of the formula ##STR4## wherein R 1 , R 2 and R 3 , which may be the same or different, represent benzyl or lower alkyl groups containing 1 to 6 carbon atoms, R 4 represents a long chain alkyl group containing from about 12 to about 22 carbon atoms and X is an anion, normally a halide, preferably a chloride.
  • Typical representatives of this class of compounds include cetyltrimethylammonium bromide and chloride, benzyldocosyldimethylammonium chloride (behenalkonium chloride), N,N,N-trimethyl-1-docosanammonium chloride (behentrimonium chloride), cetyl dimethylbenzylammonium chloride (cetalkonium chloride) and stearyl trimethylammonium chloride (steartrimonium chloride), all of which are known compounds.
  • the monomeric quaternary ammonium compounds employed in the lotions of this invention function not only as surfactants, but also as hair conditioners since under the conditions employed for hair coloring they tend to neutralize the anionic charge normally present on the keratin of human hair.
  • the compounds thus make two important contributions to the conditioning of the hair. One is that they neutralize the anionic charge on the keratin. Another is that the presence of the long chain alkyl group improves the lubricity of the hair. The conditioned hair is easy to detangle while wet. It will feel smooth and be readily managed when dry.
  • Specific quaternary ammonium compounds suitable for use in this invention are: cetyltrimethylammonium chloride, cetethyldimonium bromide, cetrimonium tosylate, behenalkonium chloride, behentrimonium chloride, cetalkonium chloride, stearalkonium chloride, steartrimonium chloride, dodecyldimethylehtylbenzyl ammonium chloride, myristalkonium chloride, and myristalkonium bromide.
  • Presently preferred quaternary ammonium compounds for use in this invention are: behentrimonium chloride, cetrimonium chloride and stearalkonium chloride.
  • the concentration of the quaternary ammonium compound in the lotion of this invention is from about 0.1% to about 5.0% by weight, preferably 0.5% to 2.0% by weight.
  • the viscosity of the completely formulated lotion of the invention when it is ready to mix with the developer is from about 1 cps to about 5000 cps, preferably 1 cps to 500 cps.
  • the lotion may contain organic solvents to assist in dissolving the dye precursors.
  • the organic solvent content should be kept at a minimum. More solvent than is necessary to dissolve the precursors may have the effect of retarding diffusion of the precursors into the hair for reaction. Accordingly, the organic solvent content of the lotion may be from 0% by weight to about 5% by weight.
  • useful solvents include alcohols containing up to three carbon atoms such as ethanol and isopropanol, polyhydroxy alcohols such as propylene or hexylene glycol and lower alkyl ethers thereof such as ethoxy ethers.
  • ком ⁇ онентs often employed in hair coloring compositions may be employed in the lotion or in the developer. These include, for example, fragrances, coloring agents and chelating agents. Antioxidants such as sodium sulfite erythroboric acid and ascorbic acid may also be included to inhibit premature oxidating.
  • the oxidizing composition or developer employed in the invention is an acidic aqueous composition which comprises the selected oxidizing agent together with one or mere anionic polymers which are insoluble in water.
  • the preferred oxidizing agent for use in the developer of the invention is hydrogen peroxide although other peroxides may be employed. These include, for example, urea peroxide, melamine peroxide, perborates and percarbonates such as sodium perborate or percarbonate.
  • the concentration of peroxide in the developer may be from about 0.5% to about 40% by weight, preferably 0.5% to 30% by weight. If the preferred hydrogen peroxide is employed, the concentration will be from about 0.5% to about 12% by weight, preferably 3% to 9% by weight.
  • anionic polymer for use in the developer. As indicated above, some anionic polymers including certain acrylate polymers tend to deactivate quaternary ammonium compounds by forming complexes.
  • anionic polymers which are insoluble in water, stable to peroxide and do not complex with and precipitate the quaternary ammonium compounds used herein. They are readily identified by a few simple tests as will be readily apparent to the skilled artisan. Suitable anionic polymers include copolymers formed from acrylic acid, and methacrylic acid lower alkyl esters of these acids as well as copolymers which include acrylamide or methacrylamide.
  • esters of acrylic polymers and polyalkylene glycol ethers of long chain fatty alcohols for example esters of acrylic polymers and polyethylene glycol ethers of stearyl alcohol such as steareth-20 represented by the formula CH 3 (CH 2 ) 16 CH 2 (OCH 2 CH 2 ) n OH wherein n has an average value of 20.
  • Anionic polymers which include homologs of stearyl alcohol such as cetyl and arachadyl alcohol or mixtures of such alcohol segments such as cetearth-20 which is based on a mixture of cetyl and stearyl alcohols may be used.
  • the presently preferred anionic polymers are alkali soluble polymers available from Rohm and Haas, Philadelphia, Pa. under the trade marks Aculyn 22 and Aculyn 33.
  • the former is believed to be a steareth-20 ester of a copolymer formed from acrylic or methacrylic acid or their lower alkyl esters. These preferred copolymers may be employed separately or together in any selected proportion.
  • the concentration of anionic polymer in the developer is from about 0.1% by weight to about 20% by weight, preferably 0.5% to 10% by weight.
  • the developer may also contain from 0 to about 0.2% by weight of a stabilizer such as phanacetin or ethylene diamine tetracetic acid (EDTA).
  • a stabilizer such as phanacetin or ethylene diamine tetracetic acid (EDTA).
  • the viscosity of the developer as prepared for mixture with the lotion is from about 1 cps to about 5000 cps by weight, preferably 1 cps to 500 cps by weight.
  • the viscosities of the lotion and the developer be close to each other. If the difference in viscosities is too great they will be difficult to mix. On shaking the thinner solution will agitate well, but the thicker component will be more difficult to agitate and the rate of blending will be slowed down.
  • the pH of the developer is from about 2 to about 6, preferably 2.5 to 4.5. Any of a variety of non-toxic acids or buffers may be employed to maintain pH. Phosphoric acid is the most preferred.
  • the lotion and developer are mixed just before application to the hair. On the hair, they form a stable gel with enough consistency and body to remain on the hair during the complete coloring period without dripping or running.
  • the primary intermediate and coupler i.e. the dye precursors diffuse rapidly into the hair together with the oxidizing agent.
  • the dyes form within the hair fiber and, since they are large molecules, remain in the hair so that the color change is permanent.
  • the term "permanent" means that the dye does not readily wash out of the hair with ordinary shampoos.
  • the color achieved with the products of this invention is so stable that it may survive as many as 20 shampoos without noticeable change.
  • the composition is washed from the hair with an ordinary water rinse followed by a shampoo.
  • compositions of this invention may be separately provided in a kit or package form ready for mixing by the user, either professional or personal, to initiate the dyeing process. It is possible to combine the lotion and the developer by mixing them directly on the hair of the user. If they are mixed on the hair, it is preferable to add the lotion first. It is preferred to mix them in a mixing vessel for subsequent application to the hair as the gel forms.
  • the kit provided in accordance with this invention comprises those containers.
  • the ingredients in the aqueous composition of the first container will include the dye precursors, the amphoteric surfactant, the quaternary ammonium compound and the alkaline reagent all in the amounts defined above.
  • the method of the invention comprises applying the mixture to the hair to be colored and allowing it to remain in contact with the hair until the desired hair color has been attained after which the composition is removed from the hair as described above.
  • the lotions and developers shown below are prepared by mixing the separate components.
  • 40 different gelled hair coloring compositions are prepared which color human hair when applied thereto and thoroughly incorporated in the hair by finger manipulation.

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US08/112,162 1993-08-26 1993-08-26 Two-part aqueous composition for coloring hair, which forms a gel on mixing of the two parts Expired - Lifetime US5376146A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
US08/112,162 US5376146A (en) 1993-08-26 1993-08-26 Two-part aqueous composition for coloring hair, which forms a gel on mixing of the two parts
CA002129473A CA2129473C (fr) 1993-08-26 1994-08-04 Composition de colorant
ZA945943A ZA945943B (en) 1993-08-26 1994-08-08 Hair coloring composition
TW083107253A TW421598B (en) 1993-08-26 1994-08-09 Hair coloring composition
JP23395794A JP3284328B2 (ja) 1993-08-26 1994-08-24 毛染組成物
SG1996001493A SG46242A1 (en) 1993-08-26 1994-08-25 Hair coloring composition
DE69429393T DE69429393T2 (de) 1993-08-26 1994-08-25 Haarfärbemittel
AT94113325T ATE210420T1 (de) 1993-08-26 1994-08-25 Haarfärbemittel
AU71454/94A AU687832B2 (en) 1993-08-26 1994-08-25 Hair coloring composition
ES94113325T ES2169055T3 (es) 1993-08-26 1994-08-25 Composicion de tinte para el cabello.
EP94113325A EP0640334B1 (fr) 1993-08-26 1994-08-25 Teinture pour cheveux
CN94115715A CN1070048C (zh) 1993-08-26 1994-08-25 染发组合物
AU67103/98A AU726857B2 (en) 1993-08-26 1998-05-20 Hair coloring composition

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US08/112,162 US5376146A (en) 1993-08-26 1993-08-26 Two-part aqueous composition for coloring hair, which forms a gel on mixing of the two parts

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US5376146A true US5376146A (en) 1994-12-27

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EP (1) EP0640334B1 (fr)
JP (1) JP3284328B2 (fr)
CN (1) CN1070048C (fr)
AT (1) ATE210420T1 (fr)
AU (1) AU687832B2 (fr)
CA (1) CA2129473C (fr)
DE (1) DE69429393T2 (fr)
ES (1) ES2169055T3 (fr)
SG (1) SG46242A1 (fr)
TW (1) TW421598B (fr)
ZA (1) ZA945943B (fr)

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US5651793A (en) * 1993-09-30 1997-07-29 Henkel Kommanditgesellschaft Auf Aktien Hydrogen peroxide preparations containing foam regulators
US5656257A (en) * 1995-04-28 1997-08-12 Electronics Hair Styling, Inc. Shampoo and conditioning composition
US5785961A (en) * 1995-03-28 1998-07-28 Shiseido Company, Ltd. Mixing-at the time of use-type hair-treating composition
US5948124A (en) * 1996-07-15 1999-09-07 Kao Corporation Composition for dyeing human hair comprising a cationic dye, a zwitterionic surfactant, and an anionic UV-absorber
US5972322A (en) * 1997-11-13 1999-10-26 Tiro Industries Incorporated System for customized hair products
US5976195A (en) * 1996-09-06 1999-11-02 L'oreal Oxidation dye composition for keratin fibers containing an oxidation dye precursor and amphiphilic polymer
US5989295A (en) * 1996-09-06 1999-11-23 L'oreal Oxidation dye composition for keratin fibres, comprising an anionic amphiphilic polymer
US5997764A (en) * 1997-12-04 1999-12-07 The B.F. Goodrich Company Thickened bleach compositions
US6010541A (en) * 1996-07-23 2000-01-04 L'oreal Oxidation dye composition for keratin fibers comprising a nonionic amphiphilic polymer
US6106578A (en) * 1998-05-06 2000-08-22 Rohm And Haas Company Hair dye compositions and method of thickening the same
US6117831A (en) * 1998-09-03 2000-09-12 Lonza Inc. Alkali metal salts of hydroxyalkyl sulfonates of aminoalkyl alkanol amines and aminoalkyl alkanol ethers and method of making same
US6156076A (en) * 1998-01-16 2000-12-05 Bristol-Myers Squibb Company Two-part hair dye compositions containing polyether polyurethanes and conditioning agents
US6187058B1 (en) 1998-05-20 2001-02-13 Combe, Inc., Low water no volatile organic compound hair lightener and dyeing composition
US6391063B1 (en) 1998-11-20 2002-05-21 L'oreal Composition for the oxidation dyeing of keratin fibers and dyeing process using this composition
US6395262B1 (en) 1996-09-20 2002-05-28 L'oreal Cosmetic composition comprising a copolymer and utilization of the copolymer in a cosmetic composition
US6395042B1 (en) 1998-11-20 2002-05-28 L'oréal Composition for the oxidation dyeing of keratin fibers and dyeing process using this composition
US20020183221A1 (en) * 2001-02-27 2002-12-05 Stanley Pohl Method for removing polymer films in the manufacture of aqueous compositions containing acrylates copolymer
US20020194683A1 (en) * 2001-05-15 2002-12-26 Stephen Casperson Two-part aqueous composition for oxidative coloration of hair
WO2003013450A2 (fr) * 2001-08-03 2003-02-20 Henkel Kommanditgesellschaft Auf Aktien Coloration selective
US6547833B2 (en) 2001-02-23 2003-04-15 Clairol Incorporated Two-part aqueous composition for oxidative coloration of hair
US20030074747A1 (en) * 2001-07-27 2003-04-24 Patricia Vuarier Composition for the oxidation dyeing of keratin fibres, comprising at least one fatty alcohol chosen from mono- and polyglycerolated fatty alcohols and a particular polyol
US20030074748A1 (en) * 2001-03-19 2003-04-24 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method and composition for the gradual permanent coloring of hair
WO2003049712A2 (fr) * 2001-12-07 2003-06-19 The Procter & Gamble Company Methode de traitement ultrasonore de cheveux et d'autres fibres keratiniques
US20030140428A1 (en) * 2001-12-28 2003-07-31 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Gradual permanent coloring of hair using dye intermediates in a shampoo base
US20030154561A1 (en) * 2001-12-28 2003-08-21 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Gradual permanent coloring of hair using dye intermediates in a shampoo base
US20030172468A1 (en) * 2002-03-13 2003-09-18 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Gradual permanent coloring of hair using dye intermediates dissolved in alkaline water with a gelling agent
US20030172470A1 (en) * 2001-02-02 2003-09-18 Laurent Chassot Colouring agents for keratin fibres containing (1.1'-biphenyl)-2.4-diamine derivatives in addition to novel (1.1'-biphenyl)-2.4-diamine-derivatives
US6641618B1 (en) 1999-01-29 2003-11-04 L'oreal S.A. Ready-to-use aqueous composition for bleaching keratin fibers, comprising a combination of a water-soluble solvent and a nonionic and/or anionic amphiphilic polymer comprising at least one fatty chain
US20030233714A1 (en) * 2000-12-13 2003-12-25 The Procter & Gamble Company Oxidative hair dye composition containing polyakyleneglycol(n)alkylamine and a solid fatty compound
US6673124B2 (en) 1998-03-06 2004-01-06 L'oreal S.A. Oxidation dyeing process and oxidation dye composition for keratin fibers which comprises a cationic amphiphilic polymer
WO2004019895A1 (fr) * 2002-08-31 2004-03-11 Wella Aktiengesellschaft Agents colorants a lustre nacre pour fibres keratineuses
US6709468B2 (en) * 2002-03-07 2004-03-23 Unilever Home & Personal Care Usa Gradual permanent coloring of hair using dye intermediates in alkaline water which contains quaternary ammonium compounds
US6736860B2 (en) * 2002-03-12 2004-05-18 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Gradual permanent coloring of hair using dye intermediates dissolved in alkaline water with fatty alcohol
US20040098816A1 (en) * 2002-11-27 2004-05-27 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Method and kit for the gradual permanent coloring of hair
US6774175B2 (en) 2001-02-16 2004-08-10 L'oreal S.A. Stabilizing compositions comprising at least two anionic associative polymers, their use for stabilization of non-solid compositions, and compositions comprising at least one stabilizing composition
US20040158941A1 (en) * 2000-04-07 2004-08-19 The Procter & Gamble Company Hair colouring and conditioning compositions
US20040158939A1 (en) * 2000-04-17 2004-08-19 The Procter & Gamble Company Phase-separated rinse-off hair coloring/conditioning products
US20040158940A1 (en) * 2000-04-17 2004-08-19 The Procter & Gamble Company Phase-separated rinse-off hair coloring/cleansing products
US20040255399A1 (en) * 2003-06-23 2004-12-23 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method and compositions for coloring hair with taurate copolymers
US20050015894A1 (en) * 2002-06-26 2005-01-27 L'oreal Composition useful for the oxidation dyeing of human keratinous fibres
US20050071933A1 (en) * 1998-08-19 2005-04-07 L'oreal S.A. Composition for dyeing keratinous fibres with a cationic direct dye and a quaternary ammonium salt
US7070769B2 (en) 2001-02-16 2006-07-04 L'oreal Compositions comprising at least two anionic associative polymers and their use for stabilization of an oxidizing solution
EP1806128A1 (fr) * 2005-12-23 2007-07-11 Henkel KGaA Produit de soin pour cheveux
US20070277331A1 (en) * 2006-06-02 2007-12-06 Ingenuity Products Llc Protecting areas of skin proximate hair or nails from hair colors/ dyes and other contaminants
EP2103299A2 (fr) 2007-11-05 2009-09-23 The Procter and Gamble Company Compositions pour la teinture d'oxydation des cheveux
GB2497886B (en) * 2012-04-02 2014-04-23 Perachem Ltd Hair treatment methods
US9364403B2 (en) 2012-04-02 2016-06-14 Perachem Limited Hair treatment methods

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DE19957947C1 (de) 1999-12-02 2001-08-09 Wella Ag Polymerkombination für Haarbehandlungsmittel
FR2803195B1 (fr) 1999-12-30 2002-03-15 Oreal Composition pour la teinture d'oxydation des fibres keratiniques comprenant un polymere epaississant comportant au moins une chaine grasse et un alcool gras mono-ou poly-glycerole
US7766976B2 (en) 2004-12-02 2010-08-03 The Procter & Gamble Company Polymer thickened hair colouring and bleaching compositions
WO2006060568A1 (fr) 2004-12-02 2006-06-08 The Procter & Gamble Company Compositions de coloration et de decoloration capillaires epaissies
DE602006016590D1 (de) 2006-07-12 2010-10-14 Procter & Gamble Auf Gelnetzwerk-Emulgatoren basierende Verdickersysteme für Haarfärbe und Haaraufhellungszusammensetzungen
JP4709725B2 (ja) * 2006-11-02 2011-06-22 花王株式会社 染毛剤組成物
MX2012006752A (es) * 2009-12-18 2012-07-04 Procter & Gamble Composicion colorante oxidativa en espuma para el cabello.
FR3008614B1 (fr) * 2013-07-19 2015-07-31 Oreal Composition de coloration comprenant un tensio actif amphotere particulier et un tensioactif sulfate
JP7198082B2 (ja) 2016-03-30 2022-12-28 日本碍子株式会社 セラミック膜フィルタ

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Cited By (80)

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Publication number Priority date Publication date Assignee Title
US5651793A (en) * 1993-09-30 1997-07-29 Henkel Kommanditgesellschaft Auf Aktien Hydrogen peroxide preparations containing foam regulators
US5785961A (en) * 1995-03-28 1998-07-28 Shiseido Company, Ltd. Mixing-at the time of use-type hair-treating composition
US5656257A (en) * 1995-04-28 1997-08-12 Electronics Hair Styling, Inc. Shampoo and conditioning composition
US5948124A (en) * 1996-07-15 1999-09-07 Kao Corporation Composition for dyeing human hair comprising a cationic dye, a zwitterionic surfactant, and an anionic UV-absorber
US6010541A (en) * 1996-07-23 2000-01-04 L'oreal Oxidation dye composition for keratin fibers comprising a nonionic amphiphilic polymer
US6344063B1 (en) 1996-07-23 2002-02-05 L'oreal Oxidation dye composition for keratin fibers comprising nonionic amphiphilic polymer
US6277155B1 (en) 1996-07-23 2001-08-21 L'oreal Oxidation dye composition for keratin fibers comprising a nonionic amphiphilic polymer
US5976195A (en) * 1996-09-06 1999-11-02 L'oreal Oxidation dye composition for keratin fibers containing an oxidation dye precursor and amphiphilic polymer
US5989295A (en) * 1996-09-06 1999-11-23 L'oreal Oxidation dye composition for keratin fibres, comprising an anionic amphiphilic polymer
US6527814B1 (en) 1996-09-06 2003-03-04 L'oreal S.A. Oxidation dye composition for keratin fibers, comprising an anionic amphiphilic polymer
US6074439A (en) * 1996-09-06 2000-06-13 L'oreal Oxidation dye composition for keratin fibers containing an oxidation dye precursor and an anionic amphiphilic polymer
US6395262B1 (en) 1996-09-20 2002-05-28 L'oreal Cosmetic composition comprising a copolymer and utilization of the copolymer in a cosmetic composition
US5993792A (en) * 1997-11-13 1999-11-30 Tiro Industries Incorporated System for customized hair products containing surfactants
US5972322A (en) * 1997-11-13 1999-10-26 Tiro Industries Incorporated System for customized hair products
US5997764A (en) * 1997-12-04 1999-12-07 The B.F. Goodrich Company Thickened bleach compositions
US6083422A (en) * 1997-12-04 2000-07-04 The B.F. Goodrich Company Thickened bleach compositions
US6156076A (en) * 1998-01-16 2000-12-05 Bristol-Myers Squibb Company Two-part hair dye compositions containing polyether polyurethanes and conditioning agents
US6673124B2 (en) 1998-03-06 2004-01-06 L'oreal S.A. Oxidation dyeing process and oxidation dye composition for keratin fibers which comprises a cationic amphiphilic polymer
US20040187230A1 (en) * 1998-03-06 2004-09-30 L'oreal S.A. Oxidation dyeing process and oxidation dye composition for keratin fibers which comprises a cationic amphiphilic polymer
US6106578A (en) * 1998-05-06 2000-08-22 Rohm And Haas Company Hair dye compositions and method of thickening the same
US6187058B1 (en) 1998-05-20 2001-02-13 Combe, Inc., Low water no volatile organic compound hair lightener and dyeing composition
US7087096B2 (en) * 1998-08-19 2006-08-08 L'oreal Composition for dyeing keratinous fibers with a cationic direct dye and a quaternary ammonium salt
US7198652B2 (en) * 1998-08-19 2007-04-03 L'oreal S.A. Composition for dyeing keratinous fibers with a cationic direct dye and a quaternary ammonium salt
US20050071933A1 (en) * 1998-08-19 2005-04-07 L'oreal S.A. Composition for dyeing keratinous fibres with a cationic direct dye and a quaternary ammonium salt
US6117831A (en) * 1998-09-03 2000-09-12 Lonza Inc. Alkali metal salts of hydroxyalkyl sulfonates of aminoalkyl alkanol amines and aminoalkyl alkanol ethers and method of making same
US6395042B1 (en) 1998-11-20 2002-05-28 L'oréal Composition for the oxidation dyeing of keratin fibers and dyeing process using this composition
US6391063B1 (en) 1998-11-20 2002-05-21 L'oreal Composition for the oxidation dyeing of keratin fibers and dyeing process using this composition
US6641618B1 (en) 1999-01-29 2003-11-04 L'oreal S.A. Ready-to-use aqueous composition for bleaching keratin fibers, comprising a combination of a water-soluble solvent and a nonionic and/or anionic amphiphilic polymer comprising at least one fatty chain
US20040158941A1 (en) * 2000-04-07 2004-08-19 The Procter & Gamble Company Hair colouring and conditioning compositions
US20040158939A1 (en) * 2000-04-17 2004-08-19 The Procter & Gamble Company Phase-separated rinse-off hair coloring/conditioning products
US20040158940A1 (en) * 2000-04-17 2004-08-19 The Procter & Gamble Company Phase-separated rinse-off hair coloring/cleansing products
US7056351B2 (en) * 2000-12-13 2006-06-06 The Procter & Gamble Company Oxidative hair dye composition containing polyakyleneglyco(n)alkylamine and a solid fatty compound
US20030233714A1 (en) * 2000-12-13 2003-12-25 The Procter & Gamble Company Oxidative hair dye composition containing polyakyleneglycol(n)alkylamine and a solid fatty compound
US7056347B2 (en) * 2001-02-02 2006-06-06 Wella Ag Coloring agents for keratin fibers containing (1,1′-biphenyl)-2,4-diamine derivatives in addition to novel (1,1′-biphenyl)-2,4-diamine-derivatives
US20030172470A1 (en) * 2001-02-02 2003-09-18 Laurent Chassot Colouring agents for keratin fibres containing (1.1'-biphenyl)-2.4-diamine derivatives in addition to novel (1.1'-biphenyl)-2.4-diamine-derivatives
US6953826B2 (en) 2001-02-16 2005-10-11 L'oreal, S.A. Multi-compartment kits comprising compositions comprising at least one stabilizing composition comprising at least two anionic associative polymers
US6774175B2 (en) 2001-02-16 2004-08-10 L'oreal S.A. Stabilizing compositions comprising at least two anionic associative polymers, their use for stabilization of non-solid compositions, and compositions comprising at least one stabilizing composition
US20040198895A1 (en) * 2001-02-16 2004-10-07 L'oreal S.A. Multi-compartment kits comprising compositions comprising at least one stabilizing composition comprising at least two anionic associative polymers
US7070769B2 (en) 2001-02-16 2006-07-04 L'oreal Compositions comprising at least two anionic associative polymers and their use for stabilization of an oxidizing solution
US6547833B2 (en) 2001-02-23 2003-04-15 Clairol Incorporated Two-part aqueous composition for oxidative coloration of hair
US6936113B2 (en) 2001-02-27 2005-08-30 The Procter & Gamble Company Method for removing polymer films in the manufacture of aqueous compositions containing acrylates copolymer
US20020183221A1 (en) * 2001-02-27 2002-12-05 Stanley Pohl Method for removing polymer films in the manufacture of aqueous compositions containing acrylates copolymer
US6984268B2 (en) 2001-02-27 2006-01-10 The Procter & Gamble Company Method for removing polymer films in the manufacture of aqueous compositions containing anionic amphiphilic polymers
US6736861B2 (en) * 2001-03-19 2004-05-18 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method and composition for the gradual permanent coloring of hair
US20030074748A1 (en) * 2001-03-19 2003-04-24 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method and composition for the gradual permanent coloring of hair
US6770103B2 (en) * 2001-03-19 2004-08-03 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method and composition for the gradual permanent coloring of hair
US20020194683A1 (en) * 2001-05-15 2002-12-26 Stephen Casperson Two-part aqueous composition for oxidative coloration of hair
EP1387661A1 (fr) * 2001-05-15 2004-02-11 P & G-Clairol, Inc. Composition aqueuse binaire pour coloration capillaire par procede oxydatif
EP1387661A4 (fr) * 2001-05-15 2005-01-26 P & G Clairol Inc Composition aqueuse binaire pour coloration capillaire par procede oxydatif
US6764523B2 (en) 2001-05-15 2004-07-20 The Procter & Gamble Company Two-part aqueous composition for oxidative coloration of hair
US20060248664A1 (en) * 2001-07-27 2006-11-09 Patricia Vuarier Composition for the oxidation dyeing of keratin fibres, comprising at least one fatty alcohol chosen from mono- and polyglycerolated fatty alcohols and a particular polyol
US7402180B2 (en) * 2001-07-27 2008-07-22 L'ORéAL S.A. Composition for the oxidation dyeing of keratin fibres, comprising at least one fatty alcohol chosen from mono- and polyglycerolated fatty alcohols and a particular polyol
US20030074747A1 (en) * 2001-07-27 2003-04-24 Patricia Vuarier Composition for the oxidation dyeing of keratin fibres, comprising at least one fatty alcohol chosen from mono- and polyglycerolated fatty alcohols and a particular polyol
WO2003013450A3 (fr) * 2001-08-03 2003-09-25 Henkel Kgaa Coloration selective
WO2003013450A2 (fr) * 2001-08-03 2003-02-20 Henkel Kommanditgesellschaft Auf Aktien Coloration selective
AU2002363970B2 (en) * 2001-12-07 2007-01-25 The Procter & Gamble Company Method for the ultrasonic treatment of hair and other keratinous fibers
US6732744B2 (en) 2001-12-07 2004-05-11 The Procter & Gamble Company Method for the ultrasonic treatment of hair and other keratinous fibers
WO2003049712A3 (fr) * 2001-12-07 2003-10-16 Procter & Gamble Methode de traitement ultrasonore de cheveux et d'autres fibres keratiniques
WO2003049712A2 (fr) * 2001-12-07 2003-06-19 The Procter & Gamble Company Methode de traitement ultrasonore de cheveux et d'autres fibres keratiniques
US6758867B2 (en) * 2001-12-28 2004-07-06 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Gradual permanent coloring of hair using dye intermediates in a shampoo base
US6726729B2 (en) * 2001-12-28 2004-04-27 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Gradual permanent coloring of hair using dye intermediates in a shampoo base
US20030154561A1 (en) * 2001-12-28 2003-08-21 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Gradual permanent coloring of hair using dye intermediates in a shampoo base
US20030140428A1 (en) * 2001-12-28 2003-07-31 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Gradual permanent coloring of hair using dye intermediates in a shampoo base
US6709468B2 (en) * 2002-03-07 2004-03-23 Unilever Home & Personal Care Usa Gradual permanent coloring of hair using dye intermediates in alkaline water which contains quaternary ammonium compounds
US6736860B2 (en) * 2002-03-12 2004-05-18 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Gradual permanent coloring of hair using dye intermediates dissolved in alkaline water with fatty alcohol
US20030172468A1 (en) * 2002-03-13 2003-09-18 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Gradual permanent coloring of hair using dye intermediates dissolved in alkaline water with a gelling agent
US6743265B2 (en) * 2002-03-13 2004-06-01 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Gradual permanent coloring of hair using dye intermediates dissolved in alkaline water with a gelling agent
US20050015894A1 (en) * 2002-06-26 2005-01-27 L'oreal Composition useful for the oxidation dyeing of human keratinous fibres
US7458993B2 (en) * 2002-06-26 2008-12-02 L'oreal Composition useful for the oxidation dyeing of human keratinous fibres
WO2004019895A1 (fr) * 2002-08-31 2004-03-11 Wella Aktiengesellschaft Agents colorants a lustre nacre pour fibres keratineuses
US20050081311A1 (en) * 2002-08-31 2005-04-21 Juergen Schmenger Pearly-lustre coloring agents for keratin fibers
US20040098814A1 (en) * 2002-11-27 2004-05-27 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method and composition for the gradual permanent coloring of hair which employ carbonates
US20040098816A1 (en) * 2002-11-27 2004-05-27 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Method and kit for the gradual permanent coloring of hair
US20040255399A1 (en) * 2003-06-23 2004-12-23 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method and compositions for coloring hair with taurate copolymers
EP1806128A1 (fr) * 2005-12-23 2007-07-11 Henkel KGaA Produit de soin pour cheveux
US20070277331A1 (en) * 2006-06-02 2007-12-06 Ingenuity Products Llc Protecting areas of skin proximate hair or nails from hair colors/ dyes and other contaminants
EP2103299A2 (fr) 2007-11-05 2009-09-23 The Procter and Gamble Company Compositions pour la teinture d'oxydation des cheveux
GB2497886B (en) * 2012-04-02 2014-04-23 Perachem Ltd Hair treatment methods
US9320695B2 (en) 2012-04-02 2016-04-26 Perachem Limited Hair treatment methods
US9364403B2 (en) 2012-04-02 2016-06-14 Perachem Limited Hair treatment methods

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AU687832B2 (en) 1998-03-05
SG46242A1 (en) 1998-02-20
AU7145494A (en) 1995-03-09
DE69429393T2 (de) 2002-08-14
EP0640334A3 (fr) 1997-03-05
EP0640334B1 (fr) 2001-12-12
CA2129473A1 (fr) 1995-02-27
ES2169055T3 (es) 2002-07-01
JP3284328B2 (ja) 2002-05-20
CN1106252A (zh) 1995-08-09
ZA945943B (en) 1995-02-13
CN1070048C (zh) 2001-08-29
DE69429393D1 (de) 2002-01-24
JPH0782123A (ja) 1995-03-28
EP0640334A2 (fr) 1995-03-01
TW421598B (en) 2001-02-11
ATE210420T1 (de) 2001-12-15
CA2129473C (fr) 2003-04-29

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